Ammonium Chloride → 3-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

HRID 1393944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1393944
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:14])[CH:12]=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.[Cl-].[NH4+]>CO.O1CCCC1.[Zn]>[F:1][C:2]1[CH:18]=[C:17]([NH2:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:14])[CH:12]=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 210816494-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine

Produkt 1

HCID 210816133-Fluoro-4-(5-methylpyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineAusbeute 92,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a heterogeneous mixture of 4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine (3.04 g, 10.55 mmol) in anhydrous methanol (60 mL) and anhydrous tetrahydrofuran (40 mL), at ambient temperature under nitrogen atmosphere, was added zinc dust (6.90 g, 105 mmol) and ammonium chloride (5.64 g, 105 mmol). The mixture was stirred for 7 h before the catalyst was filtered off and the filtrate was concentrated in vacuo to a pale yellow solid which was partitioned between chloroform and water. The aqueous layer was then extracted twice with chloroform. The combined chloroform layers were washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title compound (2.51 g, 92%) as a solid. 1H NMR (CDCl3) δ 7.86 (s, 1H), 7.64 (d, 1H, J=2.6 Hz); 7.08-7.03 (m, 1H), 6.61 (d, 1H, J=2.4 Hz), 6.55-6.45 (m, 2H), 3.78 (s, 2H), 2.60 (s, 3H); HRMS(ESI), 259.0995 (M+H)+ calc, 259.0997 (M+H)+ found.

Aufarbeitung

  1. filtrationwas filtered off
  2. concentrationthe filtrate was concentrated in vacuo to a pale yellow solid which
  3. customwas partitioned between chloroform and water
  4. extractionThe aqueous layer was then extracted twice with chloroform
  5. washThe combined chloroform layers were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-476140698d5d4230be5fe26752c500ae
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348325B2

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